Whether you’re on a first date with a promising Hinge match, meeting a new friend-crush for brunch, or hanging out as usual with your ride or die besties, sometimes we could all use a handy conversation starter to fill an awkward silence or enhance the vibes. And while you could get deep, sometimes it’s better to keep things on the lighter side. That, friends, is where this extensive list of funny questions to ask friends/dates/literally whoever you want might come in handy.
But don’t be fooled. While these questions are mostly lighthearted (and pretty hilarious, if we do say so ourselves), trading funny Qs can be as much of a bonding experience as sharing deeper or more intimate questions. In fact, according to Damona Hoffman, host of the Dates & Mates podcast, humor is one of the best ways to connect with people and ease tension, whether that means breaking the ice on a slightly awkward first date, or deepening your bond with friends and loved ones.
That doesn’t mean you have to have a tight-ten standup routine memorized before every first date or friend hang, though. According to dating coach Alexis Germany, the key to being funny is, uh, not trying too hard. Trust your own sense of humor—whether you like puns, dad jokes, or topical quips about reality TV shows—and lean into it. Just not, like too hard, ya know?
If you find yourself drawing a blank, however, tossing out one of these fun and open-ended questions is sure to get the convo started and/or assist in the event of any awkward silences that may be in need of filling. Obviously, context matters. Some of these questions are going to be better for close friends than they are crushes or coworkers, so make sure you run a vibe check before you, say, try one of the slightly more risqué options on this list at your next work happy hour. Otherwise, prepare to delight and entertain your friends, crushes, random strangers on the street, etc. with some clever inquiries. You're welcome.
1. What’s the most basic thing about you?
2. What’s the most embarrassing song you unironically love?
3. What’s your funniest misheard song lyric? “Gotta love those Starbucks lovers.”
4. What kind of drunk are you? Chatty oversharer? Sobbing disaster? Messy babe who lives for chaos?
5. Which Taylor Swift era are you? If they don’t have an answer you can’t be friends. Sorry, those are the rules.
6. What’s your worst quality according to astrology that is 100% true about you? Type A Capricorn? Weepy Pisces? Spill.
7. What’s your go-to depression meal? Dry cereal out of the box with your hands, anyone?
8. What’s the most unhinged thing you’ve done this year?
9. If you had to change your name, what would you change it to?
10. If you had to change my name, what would you change it to?
11. What’s the worst condiment? My mayo haters live for this one.
12. Most absurd social media challenge you participated in?
13. Who’s your most unhinged family member? Everybody’s got one! (And if you don’t have one, it’s you.)
14. If you got famous, what would you be famous for?
15. What’s something you’re legitimately bad at?
16. What’s one thing you hope your parents never find out about you?
17. Do you believe in ghosts?
18. Would you rather aliens or robots take over the world?
19. Which social media platform needs to die?
20. If you got canceled what would you get canceled for?
21. What’s the most cringe thing you’ve ever posted on social media?
22. If you could start a rumor about yourself, what would it be?
23. Who’s the worst celebrity couple?
24. Which celebrity do you think would actually be a good president?
25. Which celebrity do you think would be the actual worst president? Not including, ahem, a certain celebrity who has already been president.
26. Where’s the worst place to get broken up with?
27. What’s your go-to dating app opener?
28. Do the rats run this city?
29. If you could only listen to one song for the rest of your life, what would it be?
30. Which celebrity couple will be the next to break up?
31. Who would you pick to write your obituary?
32. What celebrity would play you in a movie about your life?
33. Which character from The Office are you?
34. What’s a TV show literally everyone but you has seen?
35. Let’s debate: Lana del Rey, Cancer or Gemini?
36. What genre would a movie about your life be?
37. Coke vs Pepsi? You have to compare the diet versions separately, just FYI.
38. Who’s your problematic fave?
39. Which horror movie archetype would you be? The one who suggests you split up? The woman who goes in the room she should absolutely NOT go into? The one who survives?
40. What’s the most overrated sex position?
41. What’s the most underrated sex position? Will my missionary apologists please stand up?
42. Which SATC character are you? I’m more of a Carrie Sun, Samantha Moon with a Miranda Rising.
43. If you got arrested, what crime would you have committed?
44. Who’s your celebrity hall pass?
45. Who’s your most obscure celebrity crush?
46. What’s your favorite meme of all time?
47. What would your middle school crush think if they knew you now?
48. Would you be friends with your middle school self?
49. Would you still date your middle school crush today?
50. What’s the weirdest thing you do when you’re alone?
51. What’s the weirdest thing your roommates have ever caught you doing?
52. Do you think you’re a good liar?
53. What’s one job you’re totally unqualified for but are positive you could do anyway?
54. What do you think your therapist would tell their friends about you?
55. What do you think your boss tells their friends about you?
56. If you could live in any decade other than this one, which would you pick?
57. Who’s the most overrated celebrity right now?
58. How would your third grade teacher describe you?
59. What’s the most ridiculous thing you’ve ever cried over?
60. You have to wear one of your past Halloween costumes for the rest of your life. Which one are you picking?
62. You get to switch bodies with your ex for one day. What’s the first thing you’re doing?
63. Have you ever gotten caught social media stalking someone? Sorry to the ex’s new girlfriend whose selfie from 2016 I liked that one time.
64. Be honest, how often do you social media stalk your exes?
65. Who was the first celebrity you were obsessed with as a kid? IT’S BRITNEY, BITCH.
66. If you were a cocktail, what would you be?
67. What’s the most embarrassing thing you’ve said or done while drunk?
68. Which streaming service could you not live without and which one needs to die?
69. Would you rather be 15% more attractive or 50% smarter?
70. What movie scene always makes you ugly cry?
71. What's your go-to excuse to get out of plans?
72. What’s your least favorite emoji?
73. Which emoji best encapsulates your essence? ✨✨✨
74. How long did it take you to pass your driver's test?
75. What was your worst subject in school?
76. What’s the most cringe thing anyone has ever said to you on a dating app?
77. Are you a sexy baby or a monster on the hill?
78. Which Disney Princess do you think you could win against in a fight and which one would totally kick your ass? I’m not coming for Mulan, I’ll tell you that.
79. What was your pandemic hobby? Were you making sourdough or binging Tiger King?
80. What was the last thing you googled?
81. What’s something you learned recently that you were embarrassed you didn’t already know?
82. Which would you rather reveal: your porn search history or your Grubhub history?
83. What would your presidential campaign slogan be?
84. Who would be your running mate?
85. Which historical figure would you most want to be?
86. If you had to get stuck in an elevator with one of your exes, which one would you choose?
87. If you could relive one year of your life, which one would it be?
88. Who is your fictional character crush? Mr. Darcy or Mr. Rochester?
89. Would you rather show your porn search history to your mom or your crush?
90. What’s the worst dating app?
91. Have you ever been banned from a dating app? If so, how’d it happen?
92. Are you a Kindle convert or a hard copy loyalist?
93. What was the first song/album you downloaded on your first iPod/iPhone?
94. What was the most embarrassing song on your last Spotify wrapped?
95. If you could design your own signature perfume, what would you call it?
96. Taylor Swift, Beyoncé, or Rihanna: Who’s the real queen of the music industry?
97. Which one of Henry VIII’s wives would you rather be? Alexa, play the Six soundtrack.
98. What's the one podcast you'd love to be a guest on?
99. Were you given any yearbook superlatives in high school? If not, which one *should* you have gotten?
100. What’s your social media platform of choice?
101. What’s your most irrational fear?
102. What’s the longest you’ve ever gone without sleep?
103. If you could switch lives with one person for a day, who would it be?
104. Do you think anyone has you blocked or muted on Instagram?
105. Which Kardashian/Jenner would you most want to trade lives with?
106. Which early aughts reality show would you bring back? The Simple Life or Girls Next Door?
107. Are you pro-reboots or over them?
108. What’s the weirdest rumor you’ve ever heard about yourself?
109. What was your worst first date?
110. What’s your go-to excuse to bail on plans?
111. Are you usually relieved when plans get canceled, or disappointed?
112. What was the last thing you lied about?
113. Would you rather give up ice cream or pizza?
114. What’s the cringiest Millennial trend/behavior that needs to be eliminated from this planet?
115. What is the appropriate way to text someone “okay”? K, kk, OK? So many options, so few correct ones.
116. What band would you get back together if you could?
117. What’s the weirdest gift you’ve ever received?
118. What’s the weirdest gift you’ve ever given?
119. Have you ever crashed a wedding?
120. Whose wedding would you object at? Get in loser, we’re pulling a “Speak Now.”
121. What was your funniest prank call experience?
122. What was the weirdest thing you did for fun as a kid?
123. What’s your weirdest turn-on? Dudes who keep their glasses on during sex? Just me?
124. Would you rather give up caffeine or sugar?
125. Diet Coke or Coke Zero? This one is DIVISIVE. Tread carefully.
126. How long did your longest game of Monopoly last?
127. What was your most regrettable impulse buy?
128. Which Mean Girls character most closely embodies your high school self?
129. Has anyone ever walked in on you masturbating/having sex?
130. What personal hygiene thing are you low-key kinda lazy about? Face it, none of us are flossing as much as our dentists think we are.
131. What do you lie to your doctor about?
132. What’s a lie you told your parents that you got away with?
133. What’s the most trouble you ever got in as a kid?
134. What’s one thing you’re a total pick-me about? Sorry, but we all have a few pick-me tendencies.
135. What’s the best way to break up with someone? Don’t @ me but personally I am pro breaking up over text.
136. What’s one dating app cliché you’re sick of seeing in people’s profiles? No offense, but I do not care about your dog that much.
137. You get to have your dream wedding for free, the only catch is: you have to wear your high school prom dress. Would you do it?
138. What was the nerdiest thing about you as a kid? Mathlete? Theater kid? Extensive orthodontia? We all had something.
139. What’s the most intense thing you’ve ever done to make a crush or an ex jealous?
140. Where’s the weirdest place you’ve ever had sex?
141. What’s your go-to bagel order?
142. What’s the cringiest drink someone can order at a bar?
143. What’s a sex myth you believed as a kid? Fell for ye olde “can’t get pregnant in a hot tub” myth did we?
144. What’s the most embarrassing song on your sex playlist?
145. What TV show do you think you could quote the most lines from? All I know is fine dining and SpongeBob quotes.
146. Once and for all, does pineapple belong on pizza?
147. If you could change your astrology sign, which one would you pick?
148. Why is it embarrassing to get caught taking a mirror selfie in public but not embarrassing to post that selfie on social media? Someone explain, pls.
149. What current slang term needs to be retired ASAP?
150. Who’s one celebrity you irrationally dislike for literally no reason?
151. What would you name your own signature flavor of Ben & Jerry’s?
152. Do you think your favorite high school teacher would be proud of you?
153. What’s the biggest lie you’ve ever told and gotten away with?
154. What do you think your mom was actually like at your age?
155. What’s your favorite question to ask on a first date? A question that leads to more questions! Brilliant!
156. If you were a writer or performer, what would be your pen name or stage name?
157. Who do you think you were in a past life?
158. What's your most unpopular food take?
159. What’s your worst habit?
160. Where can someone usually find you at the party? If anyone needs me I’ll be taking drunk mirror selfies in the bathroom, thanks.
161. Do you think you’re a good wedding guest?
162. Who is your dream plus-one?
163. If you could give yourself a nickname, what would it be? Word to the wise, giving yourself a nickname is cringe.
164. What’s something you don’t know how to do that most people do? Can’t ride a bike? Tie a tie?
165. What’s the most annoying thing people do at the gym?
166. Whats’s one TV show you would love to guest star on?
167. Would you let your friends set you up on a blind date?
168. What would be the theme song to the sitcom of your life?
169. What’s one movie adaptation that was actually better than the book?
170. Would you rather have five more close friends or 1,000 more Instagram followers?
171. If someone only saw your Spotify or Netflix accounts, who would they think you are?
172. Would you rather be TikTok famous or win a grammy?
173. What’s your best dad joke?
174. What was the first R-rated movie you ever saw? Who took you?
175. What’s a word you pronounced wrong your whole life?
176. Can you please tell me about your best worst school photo?
177. What was your AIM screen name? This one’s for the Millennials.
178. What was the worst middle school fashion trend you participated in? Bonus points for sharing pics.
179. What do you buy too much of but seem to never have enough of? Chapstick? Socks? Black cherry White Claw?
180. What’s the cheesiest internet pop psychology advice that actually struck a chord with you?
181. Does being an influencer sound like a dream job or a worst nightmare?
182. What’s the best WiFi name you’ve seen?
183. If you were an amateur wrestler/D-List superhero, what would your name be?
184. What’s your go-to karaoke song? “…Baby One More Time” or GTFO.
185. What’s a book you’ve never read but pretend to have read? Infinite Jest? The Odyssey? We all have one.
186. What would your vanity license plate be? Vanity plates are the marriage of niche hipster cryptic internet humor and actually funny memes that your mom would laugh at.
187. Be honest, how many hours a day do you spend on TikTok?
188. What’s something that’s embarrassing, but shouldn’t be?
189. What type of grocery store shopper are you? There’s a big difference between a list maker and an impulse buyer.
190. What’s the stupidest way you’ve ever hurt yourself? Tripped over your own feet? Got back together with a toxic ex? Could go either way!
192. What was something you believed as a kid for way too long?
193. What’s the stupidest lie you ever told as a kid?
194. What is the weirdest thing about you that most people wouldn’t guess from looking at you?
195. Socks on during sex: yea or nay?
196. How long do you wait to get up to pee when you’re watching a really good TV show?
197. What’s the grossest food thing you’ve ever done? Ate something off the floor? Amateur hour. Come talk to me when you’ve lived off day-old pizza you left out on the counter for the entirety of your college career.
198. Have you ever been sexually attracted to a cartoon character? Yes, and his name is The Guy From Mulan.
199. What would be the title of your memoir?
200. The most pressing question of our time: Is a hot dog a sandwich?
Kayla Kibbe (she/her) is the Associate Sex and Relationships Editor at Cosmopolitan US, where she covers all things sex, love, dating and relationships. She lives in Astoria, Queens and probably won’t stop talking about how great it is if you bring it up. Follow her on Twitter and Instagram.
